This may or may not be real, but The Reg is appalled at Microsoft's dirty Santa IM bot after it started talking about oral sex and dirty bastards. The transcript is above, but even IM transcripts are pretty easy to fake. We remembered the hours we spent chatting up SmarterChild in lieu of having any real friends, so we tried to reproduce this ourselves using The Reg's text:

9:38:07 AM northpole@live.com: This Microsoft Agent is powered by Windows Live Agents. Microsoft's Privacy Statement (http://go.microsoft.com/fwlink/?LinkId=74170) applies to all information which you provide to this Microsoft Agent. Please be careful about information which you provide to online services and follow safety tips, some of which can be found at http://www.microsoft.com/athome/security/default.mspx.